I prefer the outside view when speaking with good friends, because they know me well enough to gather what I'm really saying isn't 'Stop Here!' but rather 'Explain to me why I shouldn't stop here?'

Perhaps this isn't really the outside view but the trappings of the outside view used rhetorically to test whether the other party is willing to put some effort into explaining their views. The Outside View as a test of your discussion partner.

The Inside View can be a conversation halter as well; going 'farther inside' or 'farther outside' than your partner can deal with halts the conversation, not the fact that you've taken an inside/outside view by itself.

Also, am I the only one who sees clear links between Outside/inside Views and methods of avoiding the tragedies of the Anticommons/Commons? Seems like the Outside view does a good job of saying 'By continuing to gather evidence you are hurting your ability to remain rational!' while the Inside view says 'Your Grand Idea is irrational considering this evidence!'